ИСТИНА

The presence of an activated strained three-membered ring, in which the donor and acceptor fragments are located at the vicinal carbon atoms, makes DAC very attractive substrates in fine organic synthesis. In recent decades, numerous studies have been carried out on the reactivity of DA cyclopropanes towards various nitrogen-containing nucleophilic reagents, and the possibility of using these methods in the synthesis of aza-heterocyclic compounds has been explored. The reaction of nucleophilic ring-opening of DAC allows for one-step synthesizing acyclic molecules containing several nucleophilic and electrophilic centers, the subsequent pairwise interaction of which, with activation under certain conditions, makes it possible to obtain diverse cyclic compounds, including polycyclic ones with a complex ring topology. Here, we present new approaches to the preparation of various cyclic derivatives of γ-aminobutyric acid (GABA), which are privileged structures in medicinal chemistry, based on the nucleophilic ring-opening of DA cyclopropanes with anilines, benzylamines and azide ion. Methods for the synthesis of polysubstituted pyrrolidin-2-ones, tetrahydrodibenzo[c,e]pyrrolo[1,2-a]azepin-7-ones (structural analogues of the alkaloid allocolchicine), and tetrahydropyrrolo[1,2-a]quinolinones have been developed. Also, we disclosed an approach to the preparation of γ-cyanoesters, where trimethylsilyl cyanide was used as a cyanide ion surrogate. These compounds can be used as intermediates in the synthesis of a number of bioactive molecules, e.g. derivatives of aminovaleric acid, 3-arylpiperidines and a lot of substituted β-phenylethylamines.